Fluoride Anion Recognition by a Multifunctional Urea Derivative: An Experimental and Theoretical Study
Jana Schiller,
Raúl Pérez-Ruiz,
Diego Sampedro,
Eugenia Marqués-López,
Raquel P. Herrera,
David Díaz Díaz
Affiliations
Jana Schiller
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany
Raúl Pérez-Ruiz
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany
Diego Sampedro
Departamento de Química, Universidad de La Rioja, Madre de Dios, 51, Logroño 26006, Spain
Eugenia Marqués-López
Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, Zaragoza 50009, Spain
Raquel P. Herrera
Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, Zaragoza 50009, Spain
David Díaz Díaz
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany
In this work we demonstrate the ability of a multifaceted N,N′-disubstituted urea to selectively recognize fluoride anion (F−) among other halides. This additional function is now added to its already reported organocatalytic and organogelator properties. The signaling mechanism relies on the formation of a charge-transfer (CT) complex between the urea-based sensor and F¯ in the ground state with a high association constant as demonstrated by absorption and fluorescence spectroscopy. The nature of the hydrogen bonding interaction between the sensor and F¯ was established by 1H-NMR studies and theoretical calculations. Moreover, the recovery of the sensor was achieved by addition of methanol.
